DE1795772A1 - PYRIMIDINE DERIVATIVES - Google Patents

PYRIMIDINE DERIVATIVES

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DE1795772A1
DE1795772A1 DE19671795772 DE1795772A DE1795772A1 DE 1795772 A1 DE1795772 A1 DE 1795772A1 DE 19671795772 DE19671795772 DE 19671795772 DE 1795772 A DE1795772 A DE 1795772A DE 1795772 A1 DE1795772 A1 DE 1795772A1
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lower alkyl
hydroxy
dimethylamino
methyl
butyl
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DE1795772C3 (en
DE1795772B2 (en
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Richard Stewart Elias
Peter Frank Hilary Freeman
Brian Kenneth Snell
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Claims (12)

PATENTANSPRUCHS :PATENT CLAIM: und der Salze derselben, worin FL und R? für Miedrigalkyl, Jiedrigalkenyl, Niedri.^alky!phenyl, Halogenphenyl oder niedrigalkoxycarbonylsubstituiertes Phenyl, Anilino, Niedrigalkylcaroonyl, Halogen-niedrigalkylcarbonyl, ein stickstoffhaltiges nonocyclisches heterocvclisches Radikal, Phenyl-niedrigalkyl, :iiedrit-alkyl, das durch ein 6-cliedriges heterocyclischea stickstoffhaltiges Radikal substituiert ist, Cycloalkyl, Carbamoyl oder eine nitrosubstituierte Phenylsulfony!gruppeand the salts thereof, wherein FL and R ? for lower alkyl, lower alkenyl, lower alkyl, halophenyl or lower alkoxycarbonyl-substituted phenyl, anilino, lower alkylcaroonyl, halo-lower alkylcarbonyl, a nitrogen-containing nonocyclic heterocyclic radical, phenyl-lower alkyl,: iiedri t -alkyl, which is substituted by a 6-radical nitrogen-containing radical is substituted, cycloalkyl, carbamoyl or a nitro-substituted phenylsulfonyl group 509836/0917509836/0917 BAD ORIGINALBATH ORIGINAL steht; oder R1 und R~ gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden, der ein oder mehrere zusätzliche heterocyclische Atome enthalten kann, oder eine Guanidino oder -Benzylidinhydrazinogruppe bilden; R-, für Viasserstoff, Halogen, Niedrigalkyl oder Niedrigalkylthio-niedrigalkyl, steht; Rj+ für'Wasserstoff, Halogen, Niedrigalkyl, Phenyl-niedrigalkyl, Niedrigalkenyl, Niedrigalkoxyalkyl, Hydroxyhalogen-niedrigälkyl, Nitro, monocyclisch heterocyclisch substituiertes Nieürigalkyl, Phenyl, Phenyloxy oder halogen- oder niedrigalkylsubstituiertes Phenylthio, Niedrigalkylsulfonyl, pheny-niedrigalkylthio-, niedrigalkyl- oder halogensubstituiertes Phenyl-niedrigalkyl oder eine -CHO-Gruppe steht; oder R, und Rj, gemeinsam eine Niedrigalkylen- oder Niedrigalkenylenbrückengruppe bilden; X für ein Sauerstoff- oder Schwefelatom steht; und Rc für Wasserstoff, Hydroxy-niedrigalkyl, Phenyl-niedrigalkyl, Phenylcarbonyloxy-niedrigalkyl, Niedrigalkenyl, Niedrigalkoxycarbonyl-niedrigalkyl, Niedrigalkylcarbonyl-niedrigalky1, Di-niedrigalkylamino-niedrigalkyl, Niedrigalkylthio-niedrigalkyl oder Niedrigalkoxy-niedrigalkyl steht, mit der Voraussetzung, dass, wenn R^ und R? beide Methyl sind, R^ nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.stands; or R 1 and R ~ together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic ring, which can contain one or more additional heterocyclic atoms, or form a guanidino or benzylidine hydrazino group; R- is hydrogen, halogen, lower alkyl or lower alkylthio-lower alkyl; Rj + denotes hydrogen, halogen, lower alkyl, phenyl-lower alkyl, lower alkenyl, lower alkoxyalkyl, hydroxyhalogeno-lower alkyl, nitro, monocyclically heterocyclically substituted lower alkyl, phenyl, phenyloxy or halogen- or lower-alkyl-substituted phenylthio, lower alkylsulfonyl- or lower-alkyl-substituted phenylthio, lower-alkylsulfonyl or pheny-lower alkyl Phenyl-lower alkyl or a -CHO group; or R 1 and R j together form a lower alkylene or lower alkenylene bridging group; X represents an oxygen or sulfur atom; and R c represents hydrogen, hydroxy-lower alkyl, phenyl-lower alkyl, phenylcarbonyloxy-lower alkyl, lower alkenyl, lower alkoxycarbonyl-lower alkyl, lower alkylcarbonyl-lower alkyl, di-lower alkylamino-lower alkyl, lower alkylthio-lower alkyl or lower alkoxy-lower alkyl, with the proviso that, if R ^ and R ? are both methyl, R ^ is not hydrogen, halogen, allyl, butyl or azo. 2. Pyrimidinderivate der allgemeinen Formel2. Pyrimidine derivatives of the general formula R1 R2 R 1 R 2 509836/0917509836/0917 und die Salze derselben, worin R1 und R2 für Methyl, Äthyl, Propyl, Butyl, Allyl, Äthoxy, Carboxyphenyl, Anilino, Methylcarbonyl, Trifluoromethylcarbonyl, Chloromethylcarbonyl, Benzyl, 3-(4-Morpholino)-propyl, 2-Pyridyl, Cyclohexyl, Carbamoyl oder Nitrophenylsulfonyl steht; oder R1 und R2 gemeinsam mit dem-benachbarten Stickstoffatom Guanidino, Benzylidinhydrazino, Pyrrol, Morpholin, 4-Methylpiperazin, Piperidin oder einen Tetrazolring bilden; R- für Wasserstoff, Chloro, Methyl, Äthyl, Propyl, Hexyl, Äthylthiomethyl steht; Rh für Wasserstoff, Bromo, Niedrigalkyl, Benzyl, Ally, Butenyl, Äthoxyäthyl, Trichlorohydroxyäthyl, Nitro, Piperid-1-ylir.ethyl, Phenyl, Phenoxy, Chlorophenylthio, Methylphenylthio, Methylsulfonyl, Benzylthio, Dimethylbenzyl, Chlorobensyl, Dichlorobenzyl oder -CHO steht; oder R, und R^ gemeinsam eine Trimethylenbrückengruppe bilden; X für ein Sauerstoffoder Schwefelatom steht; Rn. für Wasserstoff, Hydroxyäthyl, Methoxypiethyl, Benzyl, Allyl, Methylcarboxyäthyl, Methylcarbonylmethyl, Diäthylaminoäthyl, Dimethylaminoäthyl, Äthylthioäthyl, Phenylcarbonyloxymethyl oder Äthoxyäthyl steht, mit der Voraussetzung, dass, wenn R1 und R2 beide Methyl sind, R1[I nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.and the salts thereof, in which R 1 and R 2 represent methyl, ethyl, propyl, butyl, allyl, ethoxy, carboxyphenyl, anilino, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, benzyl, 3- (4-morpholino) propyl, 2-pyridyl, Cyclohexyl, carbamoyl or nitrophenylsulfonyl; or R 1 and R 2 together with the adjacent nitrogen atom form guanidino, benzylidine hydrazino, pyrrole, morpholine, 4-methylpiperazine, piperidine or a tetrazole ring; R- represents hydrogen, chloro, methyl, ethyl, propyl, hexyl, ethylthiomethyl; Rh represents hydrogen, bromo, lower alkyl, benzyl, ally, butenyl, ethoxyethyl, trichlorohydroxyethyl, nitro, piperid-1-ylir.ethyl, phenyl, phenoxy, chlorophenylthio, methylphenylthio, methylsulfonyl, benzylthio, dimethylbenzyl, chlorobensyl or dichlorobenzyl; or R 1 and R ^ together form a trimethylene bridging group; X represents an oxygen or sulfur atom; R n . represents hydrogen, hydroxyethyl, methoxypiethyl, benzyl, allyl, methylcarboxyethyl, methylcarbonylmethyl, diethylaminoethyl, dimethylaminoethyl, ethylthioethyl, phenylcarbonyloxymethyl or ethoxyethyl, with the proviso that when R 1 and R 2 are both methyl, R 1 [I is not hydrogen, halogen , Allyl, butyl or azo. 3. Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R1 und R3 für Niedrigalkyl, Niedrigalkenyl, Niedrigalkylcarbonyl, heterocyclisches Niedrigalkyl oder Carbamoyl steht; oder R1 und R2 gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden; R-, .für Wasserstoff, Niedrigalkyl oder Niedrigalkylthio-niedrigalkyl steht; R^ für Wasserstoff, Halogen, Niedrigalkyl, Phenylniedrigalkyl, Niedrigalkenyl, Niedrigalkoxy-niedrigalkyl, Kydroxyhalogen-niedrigalkyl, eine Niedrigalkylsruppe, die durch ein stickstoffhaltiges monocyclisches heterocyclisches Radikal substituiert ist, oder Niedrigalkylsulfonyl steht; X für Sauerstoff oder Schwefel steht; und R5 für Wasserstoff, Hydroxyniedrirtalkyl, Niedrigalkylcarbonyl-niedrigalkyl, Di-niedrig-3. Pyrimidine derivatives according to claim 1, characterized in that R 1 and R 3 represent lower alkyl, lower alkenyl, lower alkylcarbonyl, heterocyclic lower alkyl or carbamoyl; or R 1 and R 2 together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic ring; R-,. For hydrogen, lower alkyl or lower alkylthio-lower alkyl; R ^ represents hydrogen, halogen, lower alkyl, phenyl-lower alkyl, lower alkenyl, lower alkoxy-lower alkyl, hydroxyhalo-lower alkyl, a lower alkyl group which is substituted by a nitrogen-containing monocyclic heterocyclic radical, or lower alkylsulfonyl; X represents oxygen or sulfur; and R 5 for hydrogen, hydroxy-lower alkyl, lower alkylcarbonyl-lower alkyl, di-lower- 509836/0917509836/0917 alkylamino-niedrigalkyl oder Niedrigalkylthio-niedrigalkyl steht, mit der Voraussetzung, dass, wenn R1 und Rp beide Methyl sind, R^ nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.alkylamino-lower alkyl or lower alkylthio-lower alkyl, with the proviso that when R 1 and Rp are both methyl, R ^ is not hydrogen, halogen, allyl, butyl or azo. 4. . Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R. und R2 für Niedrigalkyl stehen; oder R. und R2 gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden; R, für Niedrigalkyl steht; R^ für Niedrigalkyl oder Niedrigalkenyl steht; R1- für Wasserstoff steht; und X für ein Sauerstoff- oder Schwefelatom steht, mit der Voraussetzung, dass, wenn R1 und Rp beide Methyl sind, R^ nicht Allyl oder Butyl ist.4.. Pyrimidine derivatives according to claim 1, characterized in that R. and R 2 stand for lower alkyl; or R. and R 2 together with the adjacent nitrogen atom form a 5- or 6-membered heterocyclic ring; R 1 represents lower alkyl; R ^ is lower alkyl or lower alkenyl; R 1 - represents hydrogen; and X is an oxygen or sulfur atom, with the proviso that when R 1 and Rp are both methyl, then R ^ is not allyl or butyl. 5· Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R^. und Rp für Niedrigalkyl oder Niedrigalkenyl stehen; oder R1 und R_ gemeinsam mit dem benachbarten Stickstoffatom einen heterocyclischen Ring bilden; R, für Niedrigalkyl steht; R1J für Niedrigalkyl oder Niedrigalkenyl steht; R1- für Wasserstoff steht; und X für ein Sauerstoff- oder Schwefelatom steht, mit der Voraussetzung, dass, wenn R1 und R2 beide Methyl sind, R1J nicht Allyl oder Butyl ist.5 · pyrimidine derivatives according to claim 1, characterized in that R ^. and Rp is lower alkyl or lower alkenyl; or R 1 and R_ together with the adjacent nitrogen atom form a heterocyclic ring; R 1 represents lower alkyl; R 1 J represents lower alkyl or lower alkenyl; R 1 - represents hydrogen; and X is oxygen or sulfur with the proviso that when R 1 and R 2 are both methyl, then R 1 J is not allyl or butyl. 6. Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R1 und R2 für Allyl, Methyl, Äthyl, Propyl oder Butyl steht; R, für Methyl und Äthyl steht; R^ für Methyl, Äthyl, Propyl, Butyl oder Amyl steht; R5 für Wasserstoff steht und X für Sauerstoff steht.6. pyrimidine derivatives according to claim 1, characterized in that R 1 and R 2 represent allyl, methyl, ethyl, propyl or butyl; R, represents methyl and ethyl; R ^ represents methyl, ethyl, propyl, butyl or amyl; R 5 represents hydrogen and X represents oxygen. 7. Die folgenden Pyrimidinderivate: 2-Dimethylamino-4-methyl-5-n-pentyl-6-hydroxypyrimidin, 2-Dimethylamino-4-methyl-5-n-propyl-6-hydroxypyrimidin, 2-Dimethylamino-iJ-äthyl-5-n~butyl-6-hydroxypyrimidin, 2-Äthylmethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidin> 2-Diäthylamino-4-methyl-5-allyl~ö-hydroxypyrimidin,7. The following pyrimidine derivatives: 2-dimethylamino-4-methyl-5-n-pentyl-6-hydroxypyrimidine, 2-dimethylamino-4-methyl-5-n-propyl-6-hydroxypyrimidine, 2-dimethylamino- i J-ethyl -5-n ~ butyl-6-hydroxypyrimidine, 2-ethylmethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine > 2-diethylamino-4-methyl-5-allyl ~ ö-hydroxypyrimidine, 509836/0917509836/0917 2-Diäthylamino-4-methyl-5-n-butyl-6-hydroxypyrimidin, 2-Dimethylamino-4-methyl-5~äthyl-6-mercaptopyrimidin, 2-Dimethylamino-4-methyl-5-n-butyl-6-(2-dimethylaminoäthylthio)· pyrimidin,2-diethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidine, 2-dimethylamino-4-methyl-5-ethyl-6-mercaptopyrimidine, 2-Dimethylamino-4-methyl-5-n-butyl-6- (2-dimethylaminoethylthio) pyrimidine, 2-Dimethylamino-4-methyl-5~n-butyl-6-(2-diäthylaminoäthylthio)-pyrimidin, 2-dimethylamino-4-methyl-5 ~ n-butyl-6- (2-diethylaminoethylthio) pyrimidine, und die Salze derselben.and their salts. 8. Die folgenden Pyrimidinderivate:8. The following pyrimidine derivatives: 2-Dimethylamino-4-hydroxy-6-methyl~5-n-pentylpyrimidin, 2-Dimethylamino-4-hydroxy-6-methyl-5~n-propylpyrimidin, 2-Dimethylamino-5-n-hexyl-il-hydroxy-6-methylpyrimidini 2-Diraethylamino-4-äthyl-6-hydroxypyrimidin, S-Benzyl^-dimethylamino^-hydroxy-ö-methylpyrimidin, 5-n-Butyl-2-dimethylamino-4-hydroxy-β-phenylpyrirrάdin, 2-Dimethylamino-4-hydroxy-6-methyl-5-isopropylpyrimidin, 5-n-But'yl-2-di-n-butylamino-4~hydroxy~6-methylpyrimidin, 2-Diraethylamino-4-äthyIthiomethy1-6-hydroxypyrimidin, 2-Dimethy lamino-5-(2-ä thy loxy)~ät hy 1-4-hydroxy-6-r.e thy 1-pyrinidin, 2-dimethylamino-4-hydroxy-6-methyl-5-n-pentylpyrimidine, 2-dimethylamino-4-hydroxy-6-methyl-5-n-propylpyrimidine, 2-dimethylamino-5-n-hexyl- i l-hydroxy -6-methylpyrimidine i 2-diraethylamino-4-ethyl-6-hydroxypyrimidine, S-benzyl ^ -dimethylamino ^ -hydroxy-ö-methylpyrimidine, 5-n-butyl-2-dimethylamino-4-hydroxy-β-phenylpyrimidine, 2 Dimethylamino-4-hydroxy-6-methyl-5-isopropylpyrimidine, 5-n-butyl-2-di-n-butylamino-4-hydroxy-6-methylpyrimidine, 2-diraethylamino-4-ethiomethyl-6-hydroxypyrimidine , 2-Dimethy lamino-5- (2-a thy loxy) ~ ät hy 1-4-hydroxy-6-re thy 1-pyrinidine, thylairiino-^-hv'J:-c-x .■ -C rr.-.r;.r:': rL- y thy,1 arr;ino-5-St.':"''■ -·■ '■■-1Vyc'r··ox■■/■-- 6-ih":ta.T:i no-if-hy--■■■:■■· ' -; --^c-),;.:thylairiino - ^ - hv'J: -cx. ■ -C rr .-. r; .r: ' : r L- y thy, 1 arr; ino-5-St.': "'' ■ - · ■ ' ■■ - 1 Vyc'r ·· ox ■■ / ■ - 6-ih ": ta.T: i no-if-hy-- ■■■: ■■ · '- ; - ^ c -),;.: 509836/0917 BAD ORIGINAL509836/0917 BATH ORIGINAL 5-p-Chlorophenylfchio-2-dimethylamino-il-hydroxy-6-niethyl~ pyrimidin, S-n-Butyl^-dimethylamino-JJ-äthyl-o-hydroxypyrimidin, 2-Dimethylamino-4-hydroxy~6-methyl-5-p-tolylthippyrimidin, S-Benzylthio^-dimethylamino-^-hydroxy^-methylpyriinidin, S-n-Butyl^-äthylmethylamino-^-hydroxy-ö-rnethylpyrimidin, 2-Äthylmethylamino-4-hydroxy-6-methyl-5-n-propylpyrimidin, 2-Diäthylamino~4-hydroxy~6-methyl-5-n-propylpyrimidinJ 2-Dimethylamino-5-(3,4-dimethylbenzyl)-4-hydroxy-6~methylpyrimidin^ 5-p-Chlorobenzyl-2-dimethylamino-ii-hydroxy-6-methylpyrimidini 5-(3,4-Dichlorobenzyl)-2~dimethylamino-il-hydroxy-6-methylpyrimidin, 2-Diäthylamino-5"äthyl-4-hydroxy-6-methylpyrimidin, 5-Allyl-2-diäthylamino-4-hydroxy-6-methylpyrimidin, 2-Dimethylamino-5-äthyl-4-hydroxypyrimidin, 5-Allyl-2-dimethylainino-4-hydroxy-6-phenylpyriraidinJ 4-p-Chlorophenyl-2-diΓlethylamino-6-hydroxypyrimidin, 2-Dimethylamino-5-äthyl-4-hydroxy-6-phenylpyrimidin, 2-Dimethy!amino-4-hydroxy-5-p-methoxyphenylpyrimidin, 5-n-Butyl-2"dimethylamino-4-(2-hydroxyäthyloxy)-6-methylpyrimidirij 5-n-Butyl-!i~(2-diäthylaminoäthoxy)-2-dimethylamino-6-methylpyrimidirij 6-Benayloxy-2-diir;ethylaminopyrimidin, ö-AlIyloxy^-din.'ethylaminopyrimidin, 4 3 5-DimethyI -2"dirnethylamino-6- (2-hydroxyäthyloxy) -pyrimidin, 2-Dimet hy 1 amino-^-niercapto-D-methylpyrimidin, 5-n-ButyI~2"diäthyiamino-4-hydroxy-6-methylpyrimidin, 5-n-But~enyi-2~dirriethylainino"ii-hydroxy-6-methylpyrimidin, 5-n-Butyl"2~diallylamino-i|-hydroxy-6-methylpyrimidin, und die Salze davon»5-p-Chlorophenylfchio-2-dimethylamino- i l-hydroxy-6-niethyl ~ pyrimidine, Sn-butyl ^ -dimethylamino-JJ-ethyl-o-hydroxypyrimidine, 2-dimethylamino-4-hydroxy ~ 6-methyl-5- p-tolylthippyrimidine, S-benzylthio ^ -dimethylamino- ^ - hydroxy ^ -methylpyriinidine, Sn-butyl ^ -äthylmethylamino- ^ - hydroxy-ö-methylpyrimidine, 2-ethylmethylamino-4-hydroxy-6-methyl-5-n-propylpyrimidine , 2-Diethylamino ~ 4-hydroxy ~ 6-methyl-5-n-propylpyrimidine J 2-dimethylamino-5- (3,4-dimethylbenzyl) -4-hydroxy-6 ~ methylpyrimidine ^ 5-p-chlorobenzyl-2-dimethylamino - i -hydroxy-6-methylpyrimidine i 5- (3,4-dichlorobenzyl) -2 ~ dimethylamino- i l-hydroxy-6-methylpyrimidine, 2-diethylamino-5 "ethyl-4-hydroxy-6-methylpyrimidine, 5 Allyl-2-diethylamino-4-hydroxy-6-methylpyrimidine, 2-dimethylamino-5-ethyl-4-hydroxypyrimidine, 5-allyl-2-dimethylainino-4-hydroxy-6-phenylpyriraidine J 4-p-chlorophenyl-2 -diΓlethylamino-6-hydroxypyrimidine, 2-dimethylamino-5-ethyl-4-hydroxy-6-phenylpyrimidine, 2-dimethylamino-4-hydroxy-5-p-methoxyphenylpyrimidine, 5-n-butyl-2 "dim thylamino-4- (2-hydroxyäthyloxy) -6-methylpyrimidirij 5-n-butyl- ! i ~ (2-diethylaminoethoxy) -2-dimethylamino-6-methylpyrimidirij 6-benayloxy-2-diir; ethylaminopyrimidine, ö-allyloxy ^ -din.'ethylaminopyrimidine, 4 3 5-dimethyI -2 "dirnethylamino-6- (2- hydroxyäthyloxy) -pyrimidin, 2-Dimet hy 1 amino - ^ - niercapto-D-methylpyrimidin, 5-n-ButyI ~ 2 "diethyiamino-4-hydroxy-6-methylpyrimidin, 5-n-But ~ enyi-2 ~ dirriethylainino" i -hydroxy-6-methylpyrimidine, 5-n-butyl "2 ~ diallylamino-i | -hydroxy-6-methylpyrimidine, and the salts thereof» 9. Die Salze der Pyrimidinderivate nach Anspruch 9. The salts of the pyrimidine derivatives according to claim 509836/0917509836/0917 10. Die Salze der Verbindungen nach Anspruch 8.10. The salts of the compounds according to claim 8. 11. Salze nach Anspruch 9, dadurch gekennzeichnet, dass es sich um Alkalimetallsalze oder Hydrohalogenide handelt,11. Salts according to claim 9, characterized in that they are alkali metal salts or hydrohalides, 12. 5-n-Butyl-2-dimethylamino-4-hydroxy-6-niethylpyrimidin~ hydrochlorid.12. 5-n-Butyl-2-dimethylamino-4-hydroxy-6-niethylpyrimidine ~ hydrochloride. 13· Verfahren zur Herstellung der Verbindungen nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass man ein Guanidin der Formel13 · Process for the preparation of the compounds according to one of claims 1 to 12, characterized in that one Guanidine of the formula H2NH 2 N C=NHC = NH worin R^ und R2 die oben angegebenen Bedeutungen besitzen, mit einem beta-Ketoester der allgemeinen Formelwherein R ^ and R 2 have the meanings given above, with a beta-ketoester of the general formula R,.CO.CH.COORR, .CO.CH.COOR worin R-, und R21 die oben angegebenen Bedeutungen besitzen und R für eine Alkylgruppe steht, kondensiert.in which R- and R 21 have the meanings given above and R stands for an alkyl group, condensed. '/■'/ ■ < .0!"i.-;NG.H.6OHH<.0! "I .-; NG.H.6OHH 509836/0917509836/0917
DE19671795772 1966-03-31 1967-03-23 2-AMINO-4-HYDROXYPYRIMIDINE DERIVATIVES SUBSTITUTED IN THE 5- AND 6-POSITION Granted DE1795772B2 (en)

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GB1427166A GB1182584A (en) 1966-03-31 1966-03-31 Pyrimidine derivates and the use thereof as fungicides
GB1427167 1967-02-24

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DE19671795726 Expired DE1795726C3 (en) 1966-03-31 1967-03-23 2-amino-4-methyl-5-alkyl-6-hydroxy-. pyridine derivatives
DE19671795772 Granted DE1795772B2 (en) 1966-03-31 1967-03-23 2-AMINO-4-HYDROXYPYRIMIDINE DERIVATIVES SUBSTITUTED IN THE 5- AND 6-POSITION
DE19671795833 Expired DE1795833C3 (en) 1966-03-31 1967-03-23 2-Amino-6-hydroxypyrimidine derivatives substituted in the 5-position
DE19671795835 Expired DE1795835C3 (en) 1966-03-31 1967-03-23 2-Dimethylamino ^ -alkyl-e-hydroxy- or mercapto-pyrimidine derivatives substituted in the 5-position
DE1967J0033286 Granted DE1695270B2 (en) 1966-03-31 1967-03-23 AGENTS FOR CONTROLLING FUNGI IN PLANTS
DE19671795834 Pending DE1795834A1 (en) 1966-03-31 1967-03-23 FUNGICIDAL COMPOSITIONS AND METHOD FOR PREPARING THE SAME

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DE19671795835 Expired DE1795835C3 (en) 1966-03-31 1967-03-23 2-Dimethylamino ^ -alkyl-e-hydroxy- or mercapto-pyrimidine derivatives substituted in the 5-position
DE1967J0033286 Granted DE1695270B2 (en) 1966-03-31 1967-03-23 AGENTS FOR CONTROLLING FUNGI IN PLANTS
DE19671795834 Pending DE1795834A1 (en) 1966-03-31 1967-03-23 FUNGICIDAL COMPOSITIONS AND METHOD FOR PREPARING THE SAME

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US4029784A (en) * 1971-09-23 1977-06-14 Imperial Chemical Industries Limited Pyrimidine sulfamate fungicides
GB1523274A (en) 1974-08-05 1978-08-31 Ici Ltd Herbicidal compositions containing substituted pyrimidine
IT1153066B (en) * 1982-11-18 1987-01-14 Mentedison S P A HERBICIDE ACTIVITIES OF PIRIMIDIN-4-ONE
JPH0635450B2 (en) * 1984-03-16 1994-05-11 三井東圧化学株式会社 Thiocyanopyrimidine derivative, its production method and agricultural / horticultural fungicide
JPS6345269A (en) * 1986-04-28 1988-02-26 Mitsui Toatsu Chem Inc Dihalogen-substituted thiocyanopyrimidine derivative, production thereof and agricultural and horticultural fungicide
US6252076B1 (en) 1996-05-04 2001-06-26 Yuhan Corporation Process for preparation of pyrimidine derivatives
WO1998018784A1 (en) * 1996-10-29 1998-05-07 Yuhan Corporation Process for preparation of pyrimidine derivatives
IN188411B (en) 1997-03-27 2002-09-21 Yuhan Corp
WO1999031072A1 (en) * 1997-12-18 1999-06-24 E.I. Du Pont De Nemours And Company Cyclohexylamine arthropodicides and fungicides
KR100272471B1 (en) 1998-11-17 2000-11-15 김선진 Novel pyrimidine derivatives and processes for the preparation thereof
JP2010503642A (en) 2006-09-18 2010-02-04 ビーエーエスエフ ソシエタス・ヨーロピア Ternary pesticide mixture
BRPI0807012A2 (en) 2007-02-06 2014-04-22 Basf Se USE OF INSECTICIDES, METHOD OF REDUCING OR AVOIDING THE PHYTOTOXIC EFFECT OF FUNGICIDES, AND, AGENT.
EP2161259A1 (en) * 2008-09-03 2010-03-10 Bayer CropScience AG 4-Haloalkyl substituted Diaminopyrimidine
CN102461503B (en) * 2010-11-08 2013-08-14 陕西汤普森生物科技有限公司 Mandipropamid and ethirimol containing fungicides combination
WO2015036563A1 (en) 2013-09-16 2015-03-19 Bayer Pharma Aktiengesellschaft Disubstituted trifluormethyl pyrimidinones and use thereof as ccr2 antagonists

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DE1795726A1 (en) 1975-07-31
DE1795772C3 (en) 1978-06-29
AT286992B (en) 1971-01-11
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PH11586A (en) 1978-03-31
DE1795772B2 (en) 1977-11-10
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YU33661B (en) 1977-12-31
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DE1795726B2 (en) 1977-09-01
BE696470A (en) 1967-10-02
NL152855B (en) 1977-04-15
DE1695270B2 (en) 1977-05-26
DE1695270A1 (en) 1972-04-20
ES338694A1 (en) 1968-07-01
DE1795833A1 (en) 1976-03-11
DE1795833C3 (en) 1978-04-13
SE356874B (en) 1973-06-12
DE1795835A1 (en) 1976-06-24
DE1795835C3 (en) 1978-04-13
YU63067A (en) 1977-06-30
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IL27542A (en) 1975-10-15
AT276854B (en) 1969-12-10

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